Water → HCID 14877820, compound

HRID 478109Notes

Reaction equation

HRID 478109 reaction equation
[CH2:1]([O:19][CH2:20][CH:21]([CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[OH:22])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].S(OCC)(O[CH2:54][CH3:55])(=O)=O.[OH-].[Na+].O>O1CCOCC1.[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.ClCCl>[CH2:54]([O:22][CH:21]([CH2:20][O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][OH:30])[CH3:55]

Participants

8

Reactant 4

HCID 962WaterHCID 6163Diethyl SulfateHCID 14798Sodium HydroxideHCID 14373146HCID 14373146, compound

Product 1

HCID 14877820HCID 14877820, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 8154Hexadecyltrimethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

3.7 g (5.8 millimole) of 1-O-octadecyl-3-O-[2-(2-trityloxyethoxy)ethyl]glycerol and 1.5g (10 millimole) of diethyl sulfate were dissolved in 10 ml of dioxane, to which 96 mg (0.3 millimole) of cetyltrimethylammonium chloride and 2.4 g (30 millimole) of 50% sodium hydroxide were added, and the mixture was stirred at room temperature for 72 hours. Water and dichloromethane were added to the mixture and the resulting mixture was shaken for partition. Dichloromethane was distilled off and the residue was dissolved in a mixture of 20 ml of methanol and 25 ml of dioxane, to which 3 ml of concentrated hydrochloric acid was added. The mixture was stirred at 80° C. for 16 hours and then water was added to the mixture. The organic solvent was distilled off under reduced pressure, and water and ether were added to the residue. The resulting mixture was shaken for partition and ether was distilled off. The residue was purified by silica gel column chromatography (Merck Co., Art. 7734, 100 g, Eluant: hexane-ethyl acetate=3:1-1:1), to give 1.95 g (73%) of the above-captioned compound.

Workup

  1. additionwere added
  2. stirringthe resulting mixture was shaken
  3. customfor partition
  4. distillationDichloromethane was distilled off
  5. dissolutionthe residue was dissolved in a mixture of 20 ml of methanol and 25 ml of dioxane, to which 3 ml of concentrated hydrochloric acid
  6. additionwas added
  7. stirringThe mixture was stirred at 80° C. for 16 hours
  8. additionwater was added to the mixture
  9. distillationThe organic solvent was distilled off under reduced pressure, and water and ether
  10. additionwere added to the residue
  11. stirringThe resulting mixture was shaken
  12. customfor partition
  13. distillationether was distilled off
  14. customThe residue was purified by silica gel column chromatography (Merck Co., Art. 7734, 100 g, Eluant: hexane-ethyl acetate=3:1-1:1)

Sources & evidence

ORD record
ord-114fbcfd06774b638071ecbf6953d782
Source dataset
uspto-grants-1989_12
Patent number
US04889953

Reaction notes

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